Regrets
by DizneyMomma22
Summary: A short story about Will and Emma's first time together
1. The Beginning

Emma Pillsbury walks into McKinley High with her normal dimply smile on her face. Her eyes bright with joy as she bounds toward her office. The first few students she sees are staring at her in a strange way. She brushes it off, but soon realizes the hallway is full off students looking in her direction as if waiting for something to happen. It's then she sees a group of the Glee kids hugging one another. She realizes they are crying.

"Haven't you heard?" a voice next to her says happily.  
>"Heard what?" she asks a smiling Sue.<br>"Will Schuester is dead. Died in a car wreck yesterday. I finally won't have to work so hard to have him fired. God made my dreams come true in a bigger way than I could have hoped," Sue says laughing.  
>She walks away cackling as Emma's knees grow weak. She starts shaking and the school is going blurry all around her. She hears screaming and realizes it's coming from her.<p>

Popping up, her heart pounds in her chest. Looking around the room she realizes that she's in her bed. It was all a dream. She fights back the urge to call Will right at that moment. No need to wake him up, but she knew she had to see him tomorrow.

(xxxxx)

Will sits in his living room flipping through the instruction booklet before him. He scratches his head in confusion and tries once again to figure out which way the shelf was supposed to go. As he attempts to make the shelf fit, he hears a knock at the door. Getting up he brushes off the dust and debris that litter his pants as he walks to the door. Swinging it open, he is surprised to find Emma standing in front of him. She is wearing a long lime green skirt with polka dots and a matching white shirt. It makes her ginger hair look even more orange.  
>"Emma, what ... what are you doing here?" he stutters.<br>"I need to talk to you," she says nervously.  
>"Sure, come on in," he immediately replies moving aside for her to enter.<br>Walking in to the room she sees the mess on the floor and feels her chest tighten up. He must have sensed it, because he immediately apologizes.  
>"I'm sorry, I was trying to build a bookshelf. I'll clean up if you give me a few minutes," he offers bending down to pick up the mess.<br>"No. No, Will it's ok. I'd rather talk to you," she says though she reconsiders for a brief second.  
>Will's face shows concern.<br>"Come sit on the couch, please," he says holding his hand out towards the couch.  
>She walks over and sits down adjusting her skirt nervously. Will follows suit and sits down as well.<br>"What's the matter?" he asks hoping not to drag out the reason she came.  
>"I'm not sure how to begin," she says suddenly regretting her visit.<br>"Just say what's on your mind, Em," he replies.  
>"Ok, here goes nothing. I had a dream last night," she starts. She sees his eyebrows raise quickly. He obviously wasn't expecting that. "Not, one of those dreams," she clarifies. "I got to school and you were ... dead."<br>"It was just a dream," he assures her.  
>"Don't interrupt me," she says a bit too abruptly. "Please." She adds softly.<br>He nods.  
>"The thing is when I woke up I realized that there are a lot of things in my life I regret. A lot of things I wish I could change and do differently. That being said, I don't want you to be one of my regrets."<br>Her big green eyes stare back at him unsure what to do next.  
>"I'm not sure I know where this is going. Are you saying you want to give us another try?" He says hopefully.<br>"I want more than that Will. I want," she pauses and takes a deep breath. "I want to be intimate with you."  
>Her words are so soft that he can feel the struggle between her heart and mind. He reaches out and gently lays his hand on top of hers.<br>"I'm not going anywhere Emma. You don't have to rush something like this," he reassures her.  
>"That's just it Will. You can't guarantee that you won't die tomorrow. If something happened to you, I would always regret not knowing what your touch felt like. That you were not my first as I've dreamed for so long. I wouldn't be able to live with that thought," she said as her eyes showed small signs of tears.<br>Will sat silently for a few moments waiting for her to say more. He wasn't sure what to do. He wanted to wrap her up in his arms and make love to her, but at the same time he was afraid she would regret that decision.  
>"I just don't want you to do this and then find yourself wishing you would have waited," he says finally speaking up.<br>"As long as you promise to be with me all the way and I don't find out that you've been with other girls," she stops and looks at him sternly. "Then, this is what I want to do."  
>"I can assure you that there have been no other girls since Holly," he says truthfully.<br>"Then let's go," she says standing up.  
>"Now?" he says stunned.<br>"When else?"  
>"I haven't showered, or straightened up the bedroom. I don't have anything romantic to set the mood," he says suddenly realizing what a pigsty this house is.<br>"I appreciate that gesture, but I can't wait. I'm lucky I made it through the morning," she replies grabbing his hand.  
>"Emma, no. I'm not ready for this. I want to be with you and truthfully I'd take you right in the middle of my living room, but it wouldn't be right. This is your first time and I can't let you remember it like this. You have to give me some time. At least let me get myself cleaned up. You don't have to leave. You can stay here and watch TV or something," he says completely flustered by this situation.<br>"Ok, I'll give you some time, but don't keep me waiting long," she says a bit surprised by her own boldness.  
>He nods and dashes for the bedroom.<p> 


	2. The End

More than 30 minutes had passed and Emma finds herself getting more anxious every moment. She should have told him no and just got it over with. She was beginning to rethink the situation and stands up. She was going to leave. She has to leave. She couldn't do this. It wasn't the right time. Before she could make another move the bedroom door opens. Will stands in the doorway wearing a pair of fresh jeans and a red shirt that slightly hug his muscles. His hair is wet and ungeled for the first time she can remember. Her heart rate begins to slow easing her anxiety.  
>"Ok, I'm ready," he says.<br>His tone sounds so sexy to her, that she walks towards the bedroom without hesitation. When she enters the room, she sees he has straightened up the bed, lit a few candles, closed the curtains, and put a CD on softly in the background. She turns to face him, smiling nervously. He is watching her intently. She figures it's to be sure that she doesn't want to change her mind. She grabs his hand and pulls him closer to her to reassure him. Standing face to face, their bodies barely touching, she can feel the heat building between them.  
>"Will, I love you," she says looking deep into his eyes.<br>"I love you too," he replies before leaning down to kiss her lips.  
>It's a soft, gentle kiss. He pulls away after a moment and smiles at her.<br>"Are you sure? It's not too late to change your mind. I won't be mad at you," he says serious.  
>"I haven't been this sure of anything in a long time," she reponds.<br>Once again their lips touch each other only this time it is more passionate. Emma has kissed Will before, but never with tongue. She can't believe how much she enjoys this. She feels a bit embarrassed by how excited she is over a kiss that teenagers experience on a daily basis. Will suddenly stops.  
>"Don't stop," she says with her eyes closed.<br>"Emma look at me," he demands.  
>Her eyes flutter open reluctantly, but she sees the seriousness in his look.<br>"What's wrong?" she says afraid she did something wrong.  
>"Nothing's wrong sweetie. I just want you to be honest with me. You tell me if I make you uncomfortable, if I hurt you, if you feel afraid. I don't want this to be a bad experience for you," he says.<br>She nearly melts at his kind words. He really is an amazing man. She knows that he won't continue though unless she acknowledges him, so she nods her head. Not wanting to wait any longer, Emma reaches around Will's neck and pulls him back down to her lips. She feels him smile under their kiss. He is obviously amused by her eagerness. She would have been embarrassed if she weren't growing increasingly turned on. She feels Will pushing her towards the bed. When her legs reach the side, she sits down. Will still standing, lifts his shirt over his head. She gasps internally. He really is incredibly hot. His muscles and his blond hair scream to be caressed. She reaches out and runs her hands up his chest. She's done this before, but never in a moment like this. She can feel his eyes staring at her, but he lets her explore. Not rushing, not pushing, just patiently waiting. After a moment he reaches out and puts his hands on her hips. She jumps at his touch. He stops moving, but doesn't remove his hands. He waits until her eyes signal that it's ok and he slowly lifts her shirt over her head. For a brief second she panics. This is the first time someone has seen her in her bra. Her heart races as she slowly looks up at him expecting to find his eyes surveying her body. Instead they are intently looking at her. She can see he is trying to look for any sign that he should stop.  
>To her own surprise, she reaches behind her back and unhooks her bra. This time she sees him glance down, but quickly he looks back up. She smiles at him and reaches out to grab his hand. Pulling him down slightly, she places his hand on her chest. For a moment he runs his fingers gently over them. Tracing every curve and lump. Realizing that his stance and her sitting down is probably awkward for him, she pulls him down on top of her. Scooting back to be completely on the bedspread, she watches him crawl over her. He lowers his head and places kisses along her stomach trailing up to her breasts and then to her neck. She closes her eyes enjoying his advances. He wraps his arms around her body and in a swift movement she finds herself sitting on top of him.<br>She pauses for a moment not sure what to do. He gives no instructions, just stares at her lovingly. Lying back down on top of him she engulfs his mouth with hers. She feels his hands rubbing her back. One hand makes its way down to her skirt. She feels his hand make contact with her bare skin. It slowly moves its way up to her thigh where it teases her. A moan escapes her mouth. She tenses for a moment afraid of her sound, but he reassures her with a small one of his own. Will removes his hand from her thigh and places it on her hand. He guides it slowly down to his pants. He lets go when her hand reaches his buttons. She realizes he's telling her to undo his pants. She nervously attempts to do it one handed, but finds herself struggling. She gets upset and sits up looking deflated.  
>"Emma, it's ok, don't get upset," he says sitting up on his elbows.<br>"Will, I can't even undo a pair of pants. I'm so pathetic," she says climbing off of him to sit next to him.  
>"Stop that. You aren't pathetic. It's your first time and you're nervous. Listen, just lay down and I'll take care of the rest," he says unbuttoning the pants himself.<br>He immediately slips them off leaving him in just his boxers. Her look of surprise worries him.  
>"I can stop if that's what you want," he says, though she can see by the bulge in his boxers that it's not what he wants.<br>She takes a deep breath and sighs, "no. I'm ok."  
>He moves to lie down next to her and pulls her close to his body. Her head rests on his chest as he runs his fingers along her back. He makes no sexual movements. He just holds her. She realizes that he is trying to calm her down before pursuing further. She can't keep doing this to him. There's only so much understanding he can handle. With that she reaches down and pulls her skirt off leaving her in just her pink lace underwear. Will moves back a tad and looks. She sees his finger and thumb tracing the fabric. His touch is soft, but it's enough for her to start to feel a pulse down there. It's as if her body is literally screaming for him to touch it.<br>"I'm ready," she says looking into his eyes.  
>"Not quite," he says.<br>She is confused by this. She could see he was more than ready, what else needed to be done.  
>"It'll hurt less this way," he says obviously understanding her confusion.<br>She feels his fingers slip underneath the fabric. She tenses immediately. Her anxiety bursts out of her skin. He waits a few moments allowing her to get used to this. Then slowly she feels his fingers caressing her outsides. Her head tilts back into a pillow. She bites her lip enjoying his touch.  
>"Give me your other hand," she hears him say.<br>Without opening her eyes she grabs his hand. Suddenly she feels one of his fingers slip inside. She jumps and her eyes burst open. She looks into his eyes to see him staring at her concerned.  
>"Are you ok?" he asks.<br>She can't answer yet. She isn't sure if she's ok. She notices that she's squeezing his hand tightly. After a moment she feels him slowly moving the finger around. It's a bizarre feeling, but it slowly begins to feel good and hurt less. She relaxes her body again and allows him to explore her. She feels him kiss her cheek and soon he pulls his finger back out, pulling her underwear completely off as well. Once again he stares at her before making his next movement.  
>"Are you ready?" he asks.<br>She nods at him. He waits a second before taking off his boxers. She wants to look but she's afraid. She's never seen a male part before. At least, not one that was about to enter her body. He grabs her hand and moves it down to touch him. She withdrawals her hand for a second, panicking. He doesn't move or make any response. He just waits. She summons her courage and places her hand back down on him. She touches it and soon decides to look. Peaking down she sees a medium sized hard length staring back at her. She touches the soft tip and feels something warm and sticky. She snaps her hand back in surprise.  
>"Sorry," he laughs gently. "It's just a bit of pre. It's ok." He wipes it off.<br>She nods her head and places it back down. She begins to stroke it slowly. She hears him breathing a bit harder. She can tell it feels good to him. As she increases the speed in which she is touching him, she feels him pull her to his lips. Their kiss grows more passionate. She can feel his desire for her growing stronger with each flick of his tongue. Finally he pushes himself off of her.  
>"I can't take it anymore. I need to be inside of you," he says gasping for air.<br>It's the first thing he's demanded this whole time. Like being on a roller coaster, she feels that they are going up the hill right now. Her heart is racing at an incredible speed and she's wishing she could jump off the ride now, but she nods her head at him. He climbs on top of her. She feels his thickness touching her. Her brain is throwing red flags and trying desperately to get her to stop.  
>"Take a deep breath in baby," he says.<br>She obeys and instantly she feels the pain tear through her. She bites her lip so hard she's afraid she'll draw blood. She feels the tears filling her eyes.  
>"It's ok. The pain will go away," he assures her brushing one of her tears away with his finger.<br>He regrets doing this instantly.  
>"Emma, I'm sorry. I can stop," he says looking at her pained face.<br>Her eyes open allowing a load of tears to spill out.  
>"No, we've come this far. I want to finish," she says.<br>Behind the tears Will can see that she's not lying to him. So he kisses her lips a few times to reassure her, even adding one to her forehead before he slowly begins to thrust in and out. It takes a few minutes before the pain eases and she feels the pleasure of it a bit. He starts off slow in order to keep the pain at a minimum. Before long he increases his speed. The two are now joining together in moans of pleasure. As he continues to thrust into her they occasionally kiss one another lovingly. Sweat is beginning to form on Will's body. Emma would have been disgusted by this normally, but for some reason she finds herself running her fingers across the beads. His cold beads of sweat feel good against her hot body. She feels Will tensing. His legs begin to shake and he is suddenly stiff as a board. Within seconds she feels him pull of out her. She sees a pale yellowish white liquid spilling onto the bed.  
>She sits up straight, "oh dear, we have to clean that up right away."<br>Will laughs, but doesn't make any rush to move. He lies down on his stomach panting heavily. Emma is trying to tug the bedspread out from under him.  
>"Emma relax baby, I promise I'll clean it up in a second," he says not moving.<br>"I can't Will. I have to clean it up now!" She says panicking.  
>She can feel her chest tightening. He groans a bit, but rolls off the bed. She grabs the bedspread and dashes from the room. When she finally returns she sees him still lying flat on his stomach. His toned and bare behind facing the ceiling. She feels a stab of guilt. Climbing into bed next to him, she shimmies under the sheets.<br>"Sorry," she whispers.  
>His head pops up, "for what?"<br>"The bedspread," she says fingering the sheets.  
>Will just gives a small laugh and leans forward to kiss her forehead.<br>"That's why I love you. Quirks and all," he says pulling her close to him.  
>They lay silently for a while not saying anything, when Will speaks up suddenly.<br>"Well?"  
>"Well, what?" she asks.<p>

"What did you think? Was it everything you dreamed of?" he says.  
>"It hurt more than I thought it would," she replies honestly.<p>

"Yea, the first time always does. It gets easier the more you do it," he responds as he kisses her hand.

"It wasn't bad though and you were wonderful," she says trying to reassure him.

He was quiet. Moments later he broke the silence again.  
>"Do you regret it?"<br>She's quiet for a moment. She feels his confidence slipping.  
>"Only that I waited this long to be with you," she replies.<br>"Well, now you have me for as long as you want me," he says kissing her hair.  
>Emma closes her eyes feeling the happiest she's felt since she first met Will. She drifts off to sleep feeling his arms tightly around her body. Holding her for the rest of their lives.<p> 


End file.
